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A series of amides was synthesized by coupling of 3-aminomethylglaucine with various amino acid analogues. The reaction was carried out under mild conditions by using various carbodiimides and in the presence of catalytic amount of N-hydroxybenzotriazole. Five of the compounds obtained were new, and their spectral data are presented and discussed here. Selected amides were tested for their ability to scavenge the stable free 1,1-diphenyl-2-picryl-hydrazyl (DPPH●) radical. The most active compounds were N-sinapoylphenylalanyl-3-aminomethylglaucine amide and N-feruloylphenylalanyl-3-aminomethylglaucine amide and their activity was due to the presence of hydroxycinnamoyl moiety in their molecules. The compounds were further tested in vitro for antiviral activity against viruses belonging to the Picornaviridae family. Furthermore, anti-tyrosinase activity of the compounds was performed in vitro. The results obtained suggested that the most promising tyrosinase inhibitor was feruloylphenylalanyl-3-aminomethylglaucine [ABSTRACT FROM AUTHOR]